Paul Simon announced his retirement from touring in February, setting off a flurry of media coverage but not necessarily coming off as a surprise. Like Elton John, Ozzy Osbourne and more recently George Clinton, Simon announced he’d be celebrating the end of active life on the road by rousting the roadies for a string of farewell performances. It’s unlikely the Grammy-winning singer-songwriter will stay off concert stages for good, but odds are against him appearing at the Hollywood Bowl or MGM Grand Garden Arena after this year. For Simon’s fans, the prospect of having a last chance to see him live stirs feelings similar to Simon’s reaction to facing the “natural end” of his performing years: “a little unsettling, a touch exhilarating.”

Simon first stepped on the stage in junior high school along with his friend Art Garfunkel. Garfunkel had the voice, Simon had the songwriting ambition and rhythm guitar instincts, and the two became famous in their Queens neighborhood before finding chart success in the late-’50s as Tom and Jerry. They re-emerged in the next decade as folk-pop duo Simon and Garfunkel, becoming stars practically overnight when a producer added rock musicians to a singles version of “The Sound of Silence.” By 1966, they were in-demand concert draws on both sides of the Atlantic Ocean.

Although their contributions to the soundtrack of 1967’s The Graduate would secure their place in pop culture history, their partnership would dissolve in the ’70s. A 1981 reunion concert in New York City’s Central Park would be a landmark in Simon’s performing career, but he spent considerable time on tour supporting critically acclaimed albums such as Paul Simon and There Goes Rhymin’ Simon. His backing bands became ensembles that had to relate to the mélange of influences he soaked up, from reggae to samba and gospel, through his groundbreaking recording explorations. Simon’s touring performances became musical experiences.

His most daring, groundbreaking and controversial experience became the 1986 Graceland album and subsequent tour. Inspired by an African recording, Simon traveled to South Africa to record with musicians in the apartheid state. The music focused attention on a previously overlooked culture, shed light on artists such as Ladysmith Black Mambazo and essentially begat the world music genre, but Simon took some flak for not strictly abiding the cultural boycott on South Africa. The tour became historical, with Simon supported by a cast of South African musicians including Hugh Masekela, Miriam Makeba and Ladysmith.

Simon had set the bar high, but he drove himself to make subsequent tours joyous occasions. Homeward Bound—The Farewell Tour has the added element of tearful finality, with the show going on despite the December passing of Simon’s longtime guitarist Vincent Nguini. Art Garfunkel lives though, and could probably work a reunion on Central Park into his schedule as the tour draws to a close. Simon, meanwhile, gets to see if his music has a future in nightclubs following the June 1 release of Graceland—The Remixes, a dance music reimagining of his most beloved album.

MGM Grand, 8 p.m. May 27, $59.50-$175 plus tax and fee. 800.745.3000 Ticketmaster